Monoazo dyestuffs and a process for their manufacture



Patented Jan. 17, 1939 UNITED STATES PATENT OFFICE MONOAZO DYESTUFFS AND A PROCESS FOR THEIR MANUFACTURE Walter Wehrli, Basel,

Switzerland, assignor to the firm of Chemical Works Formerly Sandoz,

Basel, Switzerland No Drawing. Application March 23, 1937, Serial 6 Claims.

OCHK

wherein X represents one of the group consisting of Q and S02 and hereinall three benzene nuclei contain substituents selected from the group consisting of hydrogen, alkyl, alkoxy and halogen, with acylatedaminonaphthol sulphonic acids of thegeneral formula wherein one Y means the group and the other Y means hydrogen, whereby the benzene nucleus contains substituents selected from the group consisting of hydrogen, alkyl, alkoxy and halogen.

The same dyestuffs may also be obtained by coupling the, above cited .diazotized bases with 2-amino 8-naphthol-G-sulphonic acid or B-amino-8-naphthol-6-sulphonic acid and treating the dyestuffs thus obtained with halogenides of arcmatic carboxylic acids in order to acylate the amino group...

The dyestuffs thus obtained dye animal fibres brilliant orange to red shades of excellent fastness properties. The dyeings on wool possess an especially good fastness' to perspiration and to milling. The dyestufis can advantageously be used for dyeing natural silk from a neutral bath, as the dye baths become completely exhausted Without any addition of acids. I

One object of the present invention is, there- In Switzerland March 81, 1936 fore, the new valuable dyestufis of the general formula wherein X represents one of the group consisting of CO and S02 and one Y represents the group and the other Y means hydrogen, and wherein all four benzene nuclei contain substituents selected from the group consisting of hydrogen, alkyl, alkoxy and halogen, said dyestuffs dyeing Wool and natural silk orange or red shades of excellent fastness properties. 1

Further objects will appear hereinafter.

The following examples, without being limitative, illustrate the present invention, the parts being by weight.

. Example 1 35 parts of the base of the formula are diazotized with 6.9 parts of sodium nitrite and 25 parts of hydrochloric acid and coupled in presence of an excess of sodium acetate with 34.3 parts of Z-benzoyl-amino-8-naphthol-fi-sulphonic acid. The coupling can also be carried out in presence of sodium bicarbonate or of a similarly acting neutralizing substance. The isolated dyestufi is in dry state a red powder, dyeing wool and silk red acid is used, red dyeing dyestuffs of similar pro-perties will be obtained.

What I claim is:-

1. Monoazo-dyestufis of the general formula \N N=N NH-C 0Q l lI 2 R038 A Y Example 2 33.7 parts of thebase of the formula 0 OHrOCl are diazotized with 6.9 parts of: sodium nitrite and 25 parts of hydrochloric acid and coupled in presence of an excess of sodium acetate with 34.3

OHa O- S 0 a,

parts of 2-benzoylamino-S-naphthol-6-sulphonic which is in .dry state a. red powder, dissolving in acid. The isolated dyestufi is in dry state a red powder, dyeing wool; and. silk bluish red shades.

If in this example insteadof Z-benzoylamino- 8-naphtho1-6-sulphonic acid the 2(2',5.-dichl'orbenzoyl)amino-8-naphthol-6-sulphonic acid is water andconcentrated sulphuric acidwith' a red coloration and yielding; when dyed on animal fibre, redshades. V

3. A water-soluble azo-d'yestufi having the formula used. adyestufi. of similar properties will be obtained.

Eat-ample- 3:

30.2 parts of" the base of the formula arediazotized with 6.9 parts .of sodium nitrite and 25 parts of hydrochloric acid and coupled in presence of sodium bicarbonate with; 34 .3 parts of 3-benzoylamino- 8 naphthol 6 sulphonic acid. The isolated-:dyestufi isin dry state a red powder, dyeing wool and silk orange shades.

If instead of the. 3-benzoylamino,8-naphtholfi-sulphonic acid in this example the 3(2'-chlorbenzoylamino) -8"-naphtho1-6-sulphonic acid is employed, an orange dyeing dyestuff of similar properties results.

7 7 Example 4 33.7 parts of the base of the formula are diazotized with 6.9 parts of sodium nitrite and 25 parts of hydrochloric acid and. coupled in presence of. natrium bicarbonate with 34.3 parts of 2-henzoylamino-8-naphthol-6-sulphonic acid. The isolated dyestuff. is in drystate'a red powder, dyeing. wool andsilk red shades.

which is in dry state a red powdendi'ssol'ving in. water with; a red coloration, andin concentrated. sulphuric acid with a reddisheviolet' coloration, and yielding, when dyed on an. animal fibre, red shades.

4. A process for the manufacture of monoazodyestufls, dyeingwool and silk brilliant orange to red shades, comprising coupling a diazotized amine of the general formulawherein X. represents one member of the group consisting of hydrogen and chlorine, Y repre'-' sents: one member of the-group consisting ofhydrogen and methyl, and Z represents one member of the group consisting of-hydrogen, methyl" and methoxy, with a benzoylaminonaphthol sulphonic acid of the, formula 6. A process for the manufacture of a. monoazodyestuff, consisting in coupling the diazo compound deriving from V OCH:

wherein A stands for one member of the group consisting of hydrogen and chlorine.

5. Aprocess for the manufacture of a. monoazowith benzoylaminonaphtholsulphonic acid of the 10 dyestufi, consisting in coupling the diazo comformula,

pound deriving from V on NH-CO-O 15 0110s 0, Nam with benzoylaminonaphtholsulphonic acid of the formula 20 OH WALTER WEI-IRLI.

NaOzS 

